3-ethyl-2,3-dihydro-1H-indole

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1,6-dimethyl-4-(trifluoromethanesulphonyloxy)-2-pyridone (1.5 g, 5.5 mM) and 3-ethylindoline (1.22 g, 83 mM) was heated at an external temperature of 150° C. under argon for 3 hours. The solution was cooled. The residue was triturated with acetone to afford a solid which was collected by filtration. This solid was washed with acetone to give 1,6-dimethyl-4-(3-ethylindolin-1-yl)-2-pyridone as the hemi-trifluoromethylsulphonate salt; (1.76 g, 62% yield); m.p. 174°-175° C.; microanalysis, found C, 60.2; H, 6.0: N, 8.0%; C18H21N2. 0.5CF3SO3H requires: C, 60.1; H, 5.9; N, 8.0%: NMR (DMSOd6); 0.9-1.0(3H, t, CH2CH3), 1.4-1.6(1H, m, CHEt), 1.70-1.9(1H, m, CHEt), 2.44(3H, s, CH3), 3.25-3.4(1H, m, indoline H), 3.5(3H, s, +NCH3), 3.6-3.7(1H, m, indoline H), 4.05-4.15(1H, m, indoline H), 6.2(1H, d, pyridine CH), 6.6(1H, d, pyridine CH), 6.9-7.05(1H, t, aromatic), 7.15-7.4(3H, m, aromatic). The solution was cooled The residue was triturated with acetone to afford a solid which was collected by filtration This solid was washed with acetone

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under a nitrogen atmosphere 41 mL (41 mmol) of a 1M borane in THF solution was added dropwise to 2.2 g (14 mmol) 3-ethylidene-1,3-dihydro-indol-2-one in 50 mL THF. The reaction mixture was refluxed for 3 h and then at 0° C. mixed with 10 mL methanol followed by 15 mL semi-concentrated hydrochloric acid solution. The reaction mixture was refluxed for 3 h with stirring, cooled and washed twice with ethyl acetate. The aqueous phase was made alkaline with aqueous 4M sodium hydroxide solution and extracted three times with ethyl acetate. The organic phases were combined, dried on sodium sulphate and evaporated down. The reaction mixture was refluxed for 3 h The reaction mixture was refluxed for 3 h cooled washed twice with ethyl acetate extracted three times with ethyl acetate dried on sodium sulphate evaporated down